CN104066728A - 新有机电致发光化合物和含有该化合物的有机电致发光器件 - Google Patents
新有机电致发光化合物和含有该化合物的有机电致发光器件 Download PDFInfo
- Publication number
- CN104066728A CN104066728A CN201280067386.7A CN201280067386A CN104066728A CN 104066728 A CN104066728 A CN 104066728A CN 201280067386 A CN201280067386 A CN 201280067386A CN 104066728 A CN104066728 A CN 104066728A
- Authority
- CN
- China
- Prior art keywords
- aryl
- alkyl
- yuan
- sub
- replacement
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 84
- 238000005401 electroluminescence Methods 0.000 title claims abstract description 29
- 125000003118 aryl group Chemical group 0.000 claims description 73
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 58
- 125000001072 heteroaryl group Chemical group 0.000 claims description 45
- 229910052736 halogen Inorganic materials 0.000 claims description 29
- 150000002367 halogens Chemical class 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- -1 pyridylidene Chemical group 0.000 claims description 21
- 150000002431 hydrogen Chemical class 0.000 claims description 19
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 229910052805 deuterium Inorganic materials 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 125000005104 aryl silyl group Chemical group 0.000 claims description 12
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 9
- 229910052698 phosphorus Inorganic materials 0.000 claims description 9
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 9
- LJJQENSFXLXPIV-UHFFFAOYSA-N fluorenylidene Chemical group C1=CC=C2[C]C3=CC=CC=C3C2=C1 LJJQENSFXLXPIV-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000005110 aryl thio group Chemical group 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 5
- 229910052796 boron Inorganic materials 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- 125000001769 aryl amino group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000003968 arylidene group Chemical group [H]C(c)=* 0.000 claims 6
- 239000000463 material Substances 0.000 abstract description 57
- 238000004519 manufacturing process Methods 0.000 abstract description 7
- 230000008901 benefit Effects 0.000 abstract description 3
- 239000010410 layer Substances 0.000 description 60
- 239000002585 base Substances 0.000 description 33
- 239000011541 reaction mixture Substances 0.000 description 24
- 239000000758 substrate Substances 0.000 description 20
- 239000002019 doping agent Substances 0.000 description 18
- 239000012044 organic layer Substances 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 238000002360 preparation method Methods 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 229910052799 carbon Inorganic materials 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 230000005540 biological transmission Effects 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 7
- 150000004646 arylidenes Chemical group 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical compound C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 6
- 238000000151 deposition Methods 0.000 description 6
- 230000008021 deposition Effects 0.000 description 6
- 229910052741 iridium Inorganic materials 0.000 description 6
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 230000000903 blocking effect Effects 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- NBYLBWHHTUWMER-UHFFFAOYSA-N 2-Methylquinolin-8-ol Chemical compound C1=CC=C(O)C2=NC(C)=CC=C21 NBYLBWHHTUWMER-UHFFFAOYSA-N 0.000 description 3
- MZSAMHOCTRNOIZ-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylaniline Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(NC2=CC=CC=C2)C=CC=1 MZSAMHOCTRNOIZ-UHFFFAOYSA-N 0.000 description 3
- HAEQAUJYNHQVHV-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylbenzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NC2=CC=CC=C2)C=CC=1 HAEQAUJYNHQVHV-UHFFFAOYSA-N 0.000 description 3
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 3
- REAYFGLASQTHKB-UHFFFAOYSA-N [2-[3-(1H-pyrazol-4-yl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound N1N=CC(=C1)C=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 REAYFGLASQTHKB-UHFFFAOYSA-N 0.000 description 3
- SAHIZENKTPRYSN-UHFFFAOYSA-N [2-[3-(phenoxymethyl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound O(C1=CC=CC=C1)CC=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 SAHIZENKTPRYSN-UHFFFAOYSA-N 0.000 description 3
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 3
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 229910001507 metal halide Inorganic materials 0.000 description 3
- 150000005309 metal halides Chemical class 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
- 125000005561 phenanthryl group Chemical group 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 230000027756 respiratory electron transport chain Effects 0.000 description 3
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 3
- 125000001294 (C1-C30) cycloalkyl group Chemical group 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 2
- XNMQEEKYCVKGBD-UHFFFAOYSA-N 2-butyne Chemical compound CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 2
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical group CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 2
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 125000000842 isoxazolyl group Chemical group 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 229910052762 osmium Inorganic materials 0.000 description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 150000002910 rare earth metals Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 230000002087 whitening effect Effects 0.000 description 2
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 description 1
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- JSRLURSZEMLAFO-UHFFFAOYSA-N 1,3-dibromobenzene Chemical compound BrC1=CC=CC(Br)=C1 JSRLURSZEMLAFO-UHFFFAOYSA-N 0.000 description 1
- UCCUXODGPMAHRL-UHFFFAOYSA-N 1-bromo-4-iodobenzene Chemical compound BrC1=CC=C(I)C=C1 UCCUXODGPMAHRL-UHFFFAOYSA-N 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- BTTNYQZNBZNDOR-UHFFFAOYSA-N 2,4-dichloropyrimidine Chemical compound ClC1=CC=NC(Cl)=N1 BTTNYQZNBZNDOR-UHFFFAOYSA-N 0.000 description 1
- SSABEFIRGJISFH-UHFFFAOYSA-N 2-(2,4-difluorophenyl)pyridine Chemical compound FC1=CC(F)=CC=C1C1=CC=CC=N1 SSABEFIRGJISFH-UHFFFAOYSA-N 0.000 description 1
- VOZBMWWMIQGZGM-UHFFFAOYSA-N 2-[4-(9,10-dinaphthalen-2-ylanthracen-2-yl)phenyl]-1-phenylbenzimidazole Chemical class C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC=C(C=2C=C3C(C=4C=C5C=CC=CC5=CC=4)=C4C=CC=CC4=C(C=4C=C5C=CC=CC5=CC=4)C3=CC=2)C=C1 VOZBMWWMIQGZGM-UHFFFAOYSA-N 0.000 description 1
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 229910004261 CaF 2 Inorganic materials 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 101150003085 Pdcl gene Proteins 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- 229910003564 SiAlON Inorganic materials 0.000 description 1
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 description 1
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 125000004653 anthracenylene group Chemical group 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229910052728 basic metal Inorganic materials 0.000 description 1
- 150000003818 basic metals Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000005382 boronyl group Chemical group 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 150000004770 chalcogenides Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 125000000259 cinnolinyl group Chemical class N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000005137 deposition process Methods 0.000 description 1
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- OBISXEJSEGNNKL-UHFFFAOYSA-N dinitrogen-n-sulfide Chemical compound [N-]=[N+]=S OBISXEJSEGNNKL-UHFFFAOYSA-N 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- JKFAIQOWCVVSKC-UHFFFAOYSA-N furazan Chemical compound C=1C=NON=1 JKFAIQOWCVVSKC-UHFFFAOYSA-N 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- RTRAMYYYHJZWQK-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1 RTRAMYYYHJZWQK-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- IMKMFBIYHXBKRX-UHFFFAOYSA-M lithium;quinoline-2-carboxylate Chemical compound [Li+].C1=CC=CC2=NC(C(=O)[O-])=CC=C21 IMKMFBIYHXBKRX-UHFFFAOYSA-M 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- KPTRDYONBVUWPD-UHFFFAOYSA-N naphthalen-2-ylboronic acid Chemical compound C1=CC=CC2=CC(B(O)O)=CC=C21 KPTRDYONBVUWPD-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- TZMFJUDUGYTVRY-UHFFFAOYSA-N pentane-2,3-dione Chemical compound CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000005562 phenanthrylene group Chemical group 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- GJAWHXHKYYXBSV-UHFFFAOYSA-N quinolinic acid Chemical compound OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- 150000003527 tetrahydropyrans Chemical class 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
- C07B59/002—Heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/008—Triarylamine dyes containing no other chromophores
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/20—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2102/00—Constructional details relating to the organic devices covered by this subclass
- H10K2102/10—Transparent electrodes, e.g. using graphene
- H10K2102/101—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO]
- H10K2102/103—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO] comprising indium oxides, e.g. ITO
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Inorganic Chemistry (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
本发明涉及新颖的有机电致发光化合物以及包括该化合物的有机电致发光器件。本发明的有机电致发光化合物在制备具有长工作寿命的OLED器件上具有优势,这是因为与常规材料相比其具有高发光效率,并且通过提高的功率效率来减少功率消耗。
Description
技术领域
本发明涉及新颖的有机电致发光化合物以及含有该化合物的有机电致发光器件。
背景技术
电致发光(EL)器件是一种自发光器件,其相对于其他类型的显示器件的优势在于提供了更宽的可视角、更高的对比度并具有更快速的响应时间。伊斯曼柯达公司(Eastman Kodak)通过使用芳族二胺小分子和铝配合物作为形成发光层的材料,首先开发了一种有机EL器件[Appl.Phys.Lett.51,913,1987]。
有机EL器件中决定发光效率的最重要的因素是发光材料。迄今为止,荧光材料被广泛地用作发光材料。然而,从电致发光的机理来看,研制磷光材料是理论上将发光效率提高4倍的最好的方法之一。铱(III)络合物是众所周知的磷光材料,包括二(2-(2'-苯并噻吩基)-吡啶根合-N,C-3')(乙酰丙酮酸根合)铱((acac)Ir(btp)2)、三(2-苯基吡啶)铱(Ir(ppy)3)和二(4,6-二氟苯基吡啶合-N,C2)吡啶甲酸根合(picolinato)铱(Firpic),分别作为红色、绿色和蓝色材料。特别是近来在日本、欧洲和美国,人们正在对大量磷光材料进行研究。
迄今为止,已知4,4'-N,N'-二咔唑-联苯(CBP)是最广泛用作磷光物质的基质材料。此外,还已知有机EL器件使用浴铜灵(BCP)和二(2-甲基-8-羟基喹啉(quinolinate))(4-苯基苯酚)铝(III)(BAlq)用于空穴阻挡层;日本先锋公司(Pioneer)等开发了一种高性能有机EL器件,其采用了BAlq的衍生物作为基质材料。
虽然这些材料提供了良好的发光特性,但它们具有以下一些不足。由于它们较低的玻璃化转变温度和较差的热稳定性,当它们在真空中处于高温沉积过程时可发生降解。因为有机EL器件的功率效率是由[(π/电压)×电流效率]确定的,功率效率与电压成反比,因此必须提高功率效率从而降低功耗。虽然含有磷光材料的有机EL器件提供了比含有荧光材料的有机EL器件更高的电流效率(cd/A),但与采用荧光材料的有机EL器件相比,采用常规磷光材料(如BAlq或CBP)的有机EL器件具有更高的驱动电压。因此,采用常规磷光材料的EL器件在功率效率(lm/w)上没有优势。此外,该有机EL器件的工作寿命短。
韩国专利申请特开第2011-0014752号公开了一种基于咔唑的化合物以及使用该咔唑化合物的有机EL器件。该化合物在咔唑结构上有三个芳基作为取代基,而所述器件发射出绿光。
发明内容
技术问题
本发明的目的是提供一种有机电致发光化合物,该化合物与常规材料相比具有高发光效率和长工作寿命从而克服所述不足;以及提供一种使用所述化合物作为发光材料的有机电致发光器件,其具有高效率和长寿命。
解决问题的方法
本发明的发明人发现可以通过如下通式1表示的化合物来实现上述目的:
其中
L1表示单键、取代或未取代的(C6-C30)亚芳基、或取代或未取代的3元至30元杂亚芳基;
Ar1-Ar5各自独立地表示CR10、C-L2-(L3)m-Ar1或N,前提是Ar1-Ar5中至少一个是C-L2-(L3)m-Ar1;
L2和L3各自独立地表示取代或未取代的(C6-C30)亚芳基,或取代或未取代的3元至30元杂亚芳基;
R1、R2、R10和Ar1各自独立地表示氢、氘、卤素、取代或未取代的(C1-C30)烷基、取代或未取代的(C3-C30)环烷基、取代或未取代的5元至7元杂环烷基、取代或未取代的(C2-C30)烯基、取代或未取代的(C2-C30)炔基、取代或未取代的(C6-C30)芳基、取代或未取代的3元至30元杂芳基、-NR11R12、-SiR13R14R15、-SR16、-OR17、氰基或硝基;
R11-R17各自独立地表示氢、氘、卤素、取代或未取代的(C1-C30)烷基、取代或未取代的(C6-C30)芳基、或取代或未取代的3元至30元杂芳基;
a表示1-6的整数;当a是等于或大于2的整数时,每一个R1是相同或不同的;
b表示1-4的整数;当b是等于或大于2的整数时,每一个R2是相同或不同的;
m表示整数1或2;当m是等于或大于2的整数时,每一个L3是相同或不同的;
所述杂亚芳基、杂环烷基和杂芳基含有至少一个选自B、N、O、S、P(=O)、Si和P的杂原子;
前提是R2不是2-咔唑基或3-咔唑基。
发明的有益效果
与常规材料相比,本发明的有机电致发光化合物具有高发光效率和长工作寿命。因此,它们可用于制造具有提高的功率消耗效率的有机电致发光器件,所述提高的功率消耗效率是通过提高功率效率实现的,且该器件具有优异的工作寿命。
本发明的实施方式
下面将详细描述本发明。但是,以下描述是用于解释本发明,而不是为了以任意方式限制本发明的范围。
本发明涉及用上述通式1表示的有机电致发光化合物,包括所述有机电致发光化合物的有机电致发光材料,以及包括所述材料的有机电致发光器件。
其中,(“C1-C30)(亚)烷基”是指具有1-30个碳原子的线型或支化的(亚)烷基,其碳原子的数量优选1-20,更优选1-10,该(亚)烷基包括甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基等;“(C2-C30)烯基”是指具有2-30个碳原子的线型或支化的烯基,其碳原子的数量优选2-20,更优选2-10,该烯基包括乙烯基、1-丙烯基、2-丙烯基、1-丁烯基、2-丁烯基、3-丁烯基、2-甲基丁-2-烯基等;“(C2-C30)炔基”是指具有2-30个碳原子的线型或支化的炔基,其碳原子的数量优选2-20,更优选2-10,该炔基包括乙炔基、1-丙炔基、2-丙炔基、1-丁炔基、2-丁炔基、3-丁炔基、1-甲基戊-2-炔基等;“(C3-C30)环烷基”是指具有3-30个碳原子的单环或多环烃,其碳原子的数量优选3-20,更优选3-7,该环烷基包括环丙基、环丁基、环戊基、环己基等;“5元至7元杂环烷基”是指具有至少一个杂原子和5-7个环骨架原子的环烷基,所述杂原子选自B、N、O、S、P(=O)、Si和P,优选O、S和N,该杂环烷基包括四氢呋喃、吡咯烷、四氢噻吩(thiolan)、四氢吡喃等;“(C6-C30)(亚)芳基”是衍生自具有6-30个碳原子的芳烃的单环或稠环,其中碳原子的数量优选为6-20,更优选为6-15,该(亚)芳基包括苯基、联苯基、三联苯基、萘基、芴基、菲基、蒽基、茚基、苯并[9,10]菲基、芘基、并四苯基(tetracenyl)、苝基(perylenyl)、基(chrysenyl)、萘并萘基(naphthacenyl)、荧蒽基(fluoranthenyl)等;“3元至30元杂(亚)芳基”是具有至少一个杂原子(优选1-4个杂原子)和3-30个环骨架原子的芳基,所述杂原子选自B、N、O、S、P(=O)、Si和P;该杂(亚)芳基是单环或与至少一个苯环稠合的稠环;该杂(亚)芳基优选具有5-20个环骨架原子、更优选具有5-15个环骨架原子;该杂(亚)芳基可以是部分饱和的;该杂(亚)芳基可以通过单键将至少一个杂芳基或芳基基团与杂芳基连接形成;该杂(亚)芳基包括单环型杂芳基,包括呋喃基、噻吩基、吡咯基、咪唑基、吡唑基、噻唑基、噻二唑基、异噻唑基、异噁唑基、噁唑基、噁二唑基、三嗪基、四嗪基、***基、四唑基、呋咱基(furazanyl)、吡啶基、吡嗪基、嘧啶基、哒嗪基等;以及稠环型杂芳基,包括苯并呋喃基、苯并噻吩基、异苯并呋喃基、二苯并呋喃基、二苯并噻吩基、苯并咪唑基、苯并噻唑基、苯并异噻唑基、苯并异噁唑基、苯并噁唑基、异吲哚基、吲哚基、吲唑基、苯并噻二唑基、喹啉基、异喹啉基、噌啉基、喹唑啉基、喹喔啉基、咔唑基、吩噁嗪基、菲啶基、苯并间二氧杂环戊烯基等。此外,“卤素”包括F、Cl、Br和I。
本文所用术语“取代或未取代的”中的“取代”指的是某个官能团中的氢原子被另一个原子或基团(即取代基)取代。
通式1的L1、L2、L3、R1、R2、R10、Ar1和R11-R17基团中取代的烷基、取代的烯基、取代的炔基、取代的(亚)芳基、取代的杂(亚)芳基、取代的环(亚)烷基和取代的杂环烷基的取代基,各自独立地是至少一个选自以下的基团:氘;卤素;(C1-C30)烷基;卤代(C1-C30)烷基;(C1-C30)烷氧基;(C6-C30)芳氧基;(C6-C30)芳基;3元至30元杂芳基;被(C6-C30)芳基取代的3元至30元杂芳基;被(C1-C30)烷基和(C6-C30)芳基取代的3元至30元杂芳基;(C3-C30)环烷基;5元至7元杂环烷基;三(C1-C30)烷基甲硅烷基;三(C6-C30)芳基甲硅烷基;二(C1-C30)烷基(C6-C30)芳基甲硅烷基;(C1-C30)烷基二(C6-C30)芳基甲硅烷基;(C2-C30)烯基;(C2-C30)炔基;氰基;(C1-C30)烷硫基;(C6-C30)芳硫基;N-咔唑基;单或二(C1-C30)烷基氨基;单或二(C6-C30)芳基氨基;(C1-C30)烷基(C6-C30)芳基氨基;二(C6-C30)芳基硼基;二(C1-C30)烷基硼基(boronyl);(C1-C30)烷基(C6-C30)芳基硼基;(C6-C30)芳基(C1-C30)烷基;(C1-C30)烷基(C6-C30)芳基;羧基;硝基;和羟基。
本发明的有机电致发光化合物可由以下通式2-4表示:
其中
R1、R2、a、b、L1和A1-A5如上述通式1所定义。
具体的,L1是单键或(C6-C30)亚芳基;选自以下基团:
其中
L2和L3各自独立地表示(C6-C30)亚芳基或3元至30元杂亚芳基;
R1和R2各自独立地表示氢、氘、卤素、(C1-C30)烷基、(C6-C30)芳基或3元至30元杂芳基;
R10和Ar1各自独立地表示氢、氘、卤素、(C1-C30)烷基、(C3-C30)环烷基、(C6-C30)芳基、3元至30元杂芳基或-SiR13R14R15;
R13-R15各自独立地表示(C1-C30)烷基或(C6-C30)芳基;
a表示0-6的整数;
b表示0-4的整数;
m表示1或2的整数;以及
L1中的亚芳基,L2和L3中的亚芳基和杂亚芳基,R1和R2中的烷基、芳基和杂芳基,R10和Ar1中的烷基、环烷基、芳基和杂芳基,R13-R15中的烷基和芳基各自还可独立地被至少一个选自以下的基团取代:氘、卤素、(C1-C30)烷基、卤代(C1-C30)烷基、(C1-C30)烷氧基、(C6-C30)芳氧基、(C6-C30)芳基、3元至30元杂芳基;被(C6-C30)芳基取代的3元至30元杂芳基;被(C6-C30)芳基和(C1-C30)烷基取代的3元至30元杂芳基;(C3-C30)环烷基;三(C1-C30)烷基甲硅烷基;三(C6-C30)芳基甲硅烷基;二(C1-C30)烷基(C6-C30)芳基甲硅烷基;(C1-C30)烷基二(C6-C30)芳基甲硅烷基;氰基;(C1-C30)烷硫基;(C6-C30)芳硫基;(C6-C30)芳基(C1-C30)烷基;(C1-C30)烷基(C6-C30)芳基。
更具体的,L2表示亚苯基、亚吡啶基、亚芴基、亚咔唑基、亚二苯并呋喃基或亚二苯并噻吩基;L3表示亚苯基、亚联苯基、亚三联苯基、亚萘基、亚吡啶基、亚嘧啶基、亚芴基、亚二苯并呋喃基、亚二苯并噻吩基、亚咔唑基、5H-吡啶并[3,2-b]亚吲哚基或5H-茚并[1,2-b]亚吡啶基;Ar1表示氢、卤素、(C1-C30)烷基、(C3-C30)环烷基、(C6-C30)芳基;3元至30元杂芳基或-SiR13R14R15;R10表示氢或(C6-C30)芳基;R1和R2各自独立地表示氢、卤素、(C1-C30)烷基、(C6-C30)芳基或3元至30元杂芳基;L2中的亚苯基、亚吡啶基、亚芴基、亚咔唑基、亚二苯并呋喃基和亚二苯并噻吩基,L3中的亚苯基、亚联苯基、亚三联苯基、亚萘基、亚吡啶基、亚嘧啶基、亚芴基、亚二苯并呋喃基、亚二苯并噻吩基、亚咔唑基、5H-吡啶并[3,2-b]亚吲哚基和5H-茚并[1,2-b]亚吡啶基,Ar1中的烷基、环烷基、芳基和杂芳基,R10中的芳基,以及R1和R2中的烷基、芳基和杂芳基,各自独立地还可被至少一个选自下组的基团取代:氘、卤素、(C1-C30)烷基、卤代(C1-C30)烷基、(C1-C30)烷氧基、(C6-C30)芳氧基、(C6-C30)芳基、3元至30元杂芳基、被(C6-C30)芳基取代的3元至30元杂芳基、(C1-C30)烷硫基、(C6-C30)芳硫基、(C6-C30)芳基(C1-C30)烷基、和(C1-C30)烷基(C6-C30)芳基。
此外,L1表示单键、亚苯基、亚萘基、亚联苯基、亚三联苯基(terphenylene)、亚蒽基、亚茚基、9,9-二甲基亚芴基、亚菲基、亚苯并[9,10]菲基、亚芘基、亚苝基、亚基、亚并四苯基、亚荧蒽基、亚苯基-亚萘基(phenylene-naphthylene)、亚呋喃基、亚噻吩基、亚吡咯基、亚咪唑基、亚吡唑基、亚噻唑基、亚噻二唑基、亚异噻唑基、亚异噁唑基、亚噁唑基、亚噁二唑基、亚三嗪基、亚四嗪基、亚***基、亚呋咱基、亚吡啶基、亚吡嗪基、亚嘧啶基、亚哒嗪基、亚苯并呋喃基、亚苯并噻吩基、亚异苯并呋喃基、亚苯并咪唑基、亚苯并噻唑基、亚苯并异噻唑基、亚苯并异噁唑基、亚苯并噁唑基、亚异吲哚基、亚吲哚基、亚吲唑基、亚苯并噻二唑基、亚喹啉基、亚异喹啉基、亚噌啉基、亚喹唑啉基、亚喹喔啉基、亚菲啶基、亚苯并间二氧杂环戊烯基、亚二苯并呋喃基和亚二苯并酰苯基(dibenzocyophenylene)。
此外,R1和R2各自独立地代表氢、卤素、(C1-C30)烷基、或者选自下述的基团:
其中,R’、R”和R”’各自独立地表示(C1-C30)烷基,或(C6-C30)芳基。
此外,Ar1表示氢、卤素、(C1-C30)烷基、或者选自下述的基团:
其中R’表示卤素或(C1-C30)烷基;R”和R”’各自独立地表示(C1-C30)烷基或(C6-C30)芳基。
本发明的有机电致发光化合物包括以下化合物:
本发明的有机电致发光化合物可通过以下反应方案来制备。
[反应方案1]
其中R1,R2,a,b,L1和Ar1-Ar5如上述通式1中所定义,Hal表示卤素。
此外,本发明提供包括通式1的有机电致发光化合物的有机电致发光材料,以及包括所述材料的有机电致发光器件。所述材料可只包括本发明的有机电致发光化合物,或者还可包括通常用于有机电致发光材料的常规材料。
本发明的有机电致发光器件包括第一电极、第二电极以及所述第一电极和第二电极之间的至少一层有机层。所述有机层包含至少一种通式1的有机电致发光化合物。此外,所述有机层包括发光层,在该发光层中可使用通式1的有机电致发光化合物作为基质材料。
所述第一电极和第二电极中一个是阳极,另一个是阴极。所述有机层还包括发光层,以及至少一层选自下组的层:空穴注入层、空穴传输层、电子传输层、电子注入层、中间层和空穴阻挡层。
可在发光层中包含本发明通式1的有机电致发光化合物。当在发光层中使用本发明通式1的有机电致发光化合物时,可将该化合物作为基质材料。优选地,该发光层可包括至少一种掺杂剂。如果需要,也可包括除本发明通式1的有机电致发光化合物以外的其他化合物作为第二基质材料。
该第二基质材料可以来自任何已知的磷光基质。从发光效率来看,选自通式2-6表示的化合物的基质是特别优选的。
H-(Cz-L4)h-M (2)
H-(Cz)i-L4-M (3)
其中
Cz表示以下结构;
X表示O或S;
R21-R24各自独立地表示氢、氘、卤素、取代或未取代的(C1-C30)烷基、取代或未取代的(C6-C30)芳基、取代或未取代的5元至30元杂芳基、或R25R26R27Si-;R25-R27各自独立地表示取代或未取代的(C1-C30)烷基、或取代或未取代的(C6-C30)芳基;L4表示单键、取代或未取代的(C6-C30)亚芳基、或取代或未取代的5元至30元杂亚芳基;M表示取代或未取代的(C6-C30)芳基、或取代或未取代的5元至30元杂芳基;Y1和Y2表示-O-、-S-、-N(R31)-或-C(R32)(R33)-,前提是Y1和Y2不同时存在;R31-R33各自独立地表示取代或未取代的(C1-C30)烷基、取代或未取代的(C6-C30)芳基、取代或未取代的5元至30元杂芳基,R32和R33可以是相同的或不同的;h和i各自独立地表示1-3的整数;j、k、l和m各自独立地表示0-4的整数;当h、i、j、k、l或m是大于或等于2的整数时,每个(Cz-L4)、每个(Cz)、每个R21、每个R22、每个R23或每个R24是相同或不同的。
具体地,所述第二基质材料包括以下结构:
根据本发明,用于制备该有机电致发光器件的掺杂剂优选为一种或多种磷光掺杂剂。应用于本发明有机电致发光器件的磷光掺杂剂材料不特别限制,但可优选选自铱(Ir)、锇(Os)、铜(Cu)和铂(Pt)的络合物;更优选为铱、锇、铜和铂的邻位金属化的(ortho-metallated)络合物;更优选为铱的邻位金属化的络合物。
根据本发明,包含在有机电致发光器件中的掺杂剂可以选自由下述通式7-9表示的化合物:
其中
L选自以下结构:
R100表示氢、取代或未取代的(C1-C30)烷基、或取代或未取代的(C1-C30)环烷基;R101-R109和R111-R123各自独立地表示氢、氘、卤素、未取代或被卤素取代的(C1-C30)烷基、取代或未取代的(C1-C30)环烷基、氰基、或取代或未取代的(C1-C30)烷氧基;R120-R123与相邻取代基相连以形成稠环,如喹啉;R124-R127各自独立地表示氢、氘、卤素、取代或未取代的(C1-C30)烷基、或取代或未取代的(C6-C30)芳基;当R124-R127是芳基时,它们可与相邻取代基连接以形成稠环,如芴;R201-R211各自独立地表示氢、氘、卤素、未取代或被卤素取代的(C1-C30)烷基、或取代或未取代的(C3-C30)环烷基;f和g各自独立地表示1-3的整数;当f或g是大于或等于2的整数时,每个R100是相同或不同的;n是1-3的整数。
所述掺杂剂材料包括以下物质:
本发明还提供一种用于有机电致发光器件的材料。所述材料包括第一基质材料和第二基质材料;所述第一基质材料可包含本发明的有机电致发光化合物。所述第一基质材料和第二基质材料的重量比可以为1:99-99:1。
此外,本发明的有机电致发光器件包括第一电极、第二电极、以及在所述第一和第二电极之间的至少一层有机层,所述有机层包括发光层,该发光层包括用于本发明有机电致发光器件的材料和磷光掺杂剂材料。将用于有机电致发光器件的材料用作基质材料。
本发明的有机电致发光器件包括通式1表示的有机电致发光化合物,还可包括至少一种选自基于芳胺的化合物和基于苯乙烯基芳胺的化合物的化合物。
在本发明的有机电致发光器件中,除了通式1表示的有机电致发光化合物之外,所述有机层还可包含至少一种选自元素周期表第1族金属、第2族金属、第四周期过渡金属、第五周期过渡金属、镧系金属和d-过渡元素的有机金属的金属,或者至少一种包含所述金属的配合物。所述有机层可包括发光层和电荷产生层。
此外,除了本发明的有机电致发光化合物之外,所述有机电致发光器件可通过进一步包含至少一层发光层来发射白光,所述发光层包含蓝光电致发光化合物、红光电致发光化合物或者绿光电致发光化合物。
根据本发明,有机电致发光器件中,可以在一个或两个电极的内表面上放置至少一层优选选自硫属化物层、金属卤化物层和金属氧化物层的层(以下称为“表面层”)。具体地,优选将硅或铝的硫属化物(包括氧化物)层放置在电致发光介质层的阳极表面上,将金属卤化物层或金属氧化物层放置在电致发光介质层的阴极表面上。所述表面层为有机电致发光器件提供了工作稳定性。优选地,所述硫属化物包括SiOX(1≤X≤2)、AlOX(1≤X≤1.5)、SiON、SiAlON等;所述金属卤化物包括LiF、MgF2、CaF2、稀土金属氟化物等;所述金属氧化物包括Cs2O、Li2O、MgO、SrO、BaO、CaO等。
优选地,在本发明的有机电致发光器件中,电子传输化合物和还原性掺杂剂的混合区或者空穴传输化合物和氧化性掺杂剂的混合区可放置在电极对中的至少一个表面上。在这种情况下,电子传输化合物被还原成阴离子,这样电子从混合区注入并传输到电致发光介质中变得更加容易。此外,空穴传输化合物被氧化成阳离子,从而空穴从混合区注入并传输到电致发光介质中变得更加容易。优选地,所述氧化性掺杂剂包括各种路易斯酸和受体化合物;所述还原性掺杂剂包括碱金属、碱金属化合物、碱土金属、稀土金属及其混合物。可以采用还原性掺杂剂层作为电荷产生层来制备具有两层或更多层电致发光层并发射白光的电致发光器件。
至于构成本发明有机电致发光器件的层的形成,可采用干成膜法如真空蒸镀、溅射、等离子和离子电镀方法等,或湿成膜法如旋涂、浸涂、流涂方法等。
当采用湿成膜法时,可通过将构成每层的材料溶解或分散至合适溶剂中来形成薄膜,所述溶剂例如乙醇、氯仿、四氢呋喃、二噁烷等。所述溶剂没有特别限制。
下文参照本发明的代表化合物详细描述所述有机电致发光化合物、所述化合物的制备方法、以及包含本发明化合物的器件的发光性质:
实施例1:化合物C-31的制备
化合物1-1的制备
将1-溴-2-硝基苯(50.0g,0.247mol)、萘-2-基硼酸(64.0g,0.37mol)、四(三苯基膦)钯(0)[Pd(PPh3)4](14.0g,0.012mol)、Na2CO3(81.0g,0.60mol)、甲苯(1000mL)、EtOH(500mL)和H2O(200mL)加入到2000mL圆底烧瓶中后,在60℃下将该反应混合物搅拌12小时。反应完成后,用乙酸乙酯萃取该反应混合物。得到的有机层用MgSO4干燥并过滤,并在减压下从该层中去除溶剂。通过柱分离所得有机层,以得到白色固体化合物1-1(37g,60%)。
化合物1-2的制备
将化合物1-1(37g,0.14mol)和亚磷酸三乙酯[P(OEt)3](180mL)添加至干燥的250mL圆底烧瓶中后,将该反应混合物搅拌19个小时。反应完成后,将该反应混合物蒸馏以去除P(OEt)3,并通过柱分离以得到黄色固体化合物1-2(17g,52%)。
化合物1-3的制备
将化合物1-2(17.4g,1mol),1-溴-4-碘苯(45.3g,2mol)、CuI(7.63g,0.5mol)、乙二胺(EDA)(5.4mL,2mol)、K2CO3(51g,3mol)和甲苯(400mL)添加至2000ml圆底烧瓶中后,在110℃下将该反应混合物搅拌12小时。反应完成后,用二氯甲烷萃取该反应混合物。得到的有机层用MgSO4干燥并过滤,并在减压下从该层中去除溶剂。通过柱分离所得有机层,以得到白色固体化合物1-3(17.3g,58%)。
化合物1-4的制备
将四氢呋喃(THF)(350mL)和化合物1-3(17.3g,1mol)添加至干燥的3000mL圆底烧瓶中后,在N2保护下搅拌该反应混合物并将其冷却至-78℃。将正丁基锂(n-BuLi)(28mL,2.5M在己烷中的溶液)缓慢加入到该反应混合物中。在-78℃下搅拌该反应混合物1个小时,在-78℃下向该反应混合物中缓慢加入三异丙醇硼[B(O-iPr)3](21mL,2mol),并在室温下搅拌该反应混合物12小时。反应完成后,用乙酸乙酯萃取反应混合物。得到的有机层用MgSO4干燥并过滤,并在减压下从该层中去除溶剂。用二氯甲烷和己烷对所述有机层进行重结晶,得到白色化合物1-4(10g,64%)。
化合物1-5的制备
将(1,1’-联苯基)-4-基硼酸(1.3kg,6.5mol)、1,3-二溴苯(2L,16.4mol)、二氯双(三苯基膦)钯(II)[PdCl2(PPh3)2](138g,0.20mol)、Na2CO3(1.74kg,16.41mol)、甲苯(12L)、EtOH(2L)和H2O(8L)添加至20L圆底烧瓶中后,在120℃下将该反应混合物搅拌12小时。反应完成后,用乙酸乙酯萃取该反应混合物。得到的有机层用MgSO4干燥并过滤,并在减压下从该层中去除溶剂。用乙酸乙酯对所述有机层进行重结晶,得到白色化合物1-5(820g,40%)。
化合物1-6的制备
将THF(16L)和化合物1-5(820g,2.66mol)添加至干燥的20L圆底烧瓶中后,在N2保护下搅拌该反应混合物并将其冷却至-78℃。将n-BuLi(28L,2.5M在己烷中的溶液)缓慢加入到该反应混合物中。在-78℃下搅拌该反应混合物1个小时,在-78℃下向该反应混合物中缓慢加入三甲氧基硼烷(trimethoxyborane)[B(OMe)3](444mL,3.99mol),并在室温下搅拌该反应混合物12小时。反应完成后,用乙酸乙酯萃取反应混合物。得到的有机层用MgSO4干燥并过滤,并在减压下从该层中去除溶剂。用己烷对所得有机层进行重结晶,得到白色固体化合物1-6(587g,81%)。
化合物1-7的制备
将2,4-二氯嘧啶(478g,3.2mol)、化合物1-6(587g,2.14mol)、Pd(PPh3)4(99g,0.08mol)、Na2CO3(567g,5.35mol)、甲苯(8L)、EtOH(2.7L)和H2O(2.7L)添加至20L圆底烧瓶后,在120℃下将该反应混合物搅拌12小时。反应完成后,用二甲基甲酰胺(DMF)对该反应混合物进行萃取和重结晶,得到化合物1-7(535g,73%)。
化合物C-31的制备
将化合物1-7(9.8g,0.028mol)、化合物1-4(8g,0.024mol)、Pd(PPh3)4(1.37g,0.001mol)、K2CO3(9.83g,0.07mol)、甲苯(120L)、EtOH(30mL)和H2O(36mL)添加至500mL圆底烧瓶后,在120℃下将该反应混合物搅拌12小时。反应完成后,用己烷对该反应混合物进行重结晶,得到化合物C-31(4.5g,26%)。
MS/FAB的实测值599.72;计算值599.24
器件实施例1:使用本发明有机电致发光化合物的OLED器件的制造
使用本发明的化合物来制造OLED器件。用三氯乙烯、丙酮、乙醇和蒸馏水依次对用于有机发光二极管(OLED)器件的玻璃基材上的透明电极氧化铟锡(ITO)薄膜(15Ω/sq)(韩国三星康宁公司(Samsung Corning))进行超声清洗,然后储存在异丙醇中。接着,将ITO基材安装在真空气相沉积设备的基材夹具(holder)上。将N4,N4-二(4-萘-2-基(N-苯基)氨基)苯基)-N1-(萘-2-基)-N1-苯基苯-1,4-二胺引入所述真空气相沉积设备的室中,然后将所述设备的室压控制在10-6托。接着,向所述室施加电流以蒸发上述引入的物质,从而在ITO基材上形成厚度为60nm的空穴注入层。然后,将N,N’-二(4-联苯基)-N,N’-二(4-联苯基)-4,4’-二氨基联苯引入所述真空气相沉积设备的另一个室中,通过向该室施加电流以进行蒸发,从而在所述空穴注入层上形成厚度为20nm的空穴传输层。形成空穴注入层和空穴传输层,随后在其上气相沉积一层发光层。之后,将化合物C-31引入真空气相沉积设备的一个室中作为基质材料,并将化合物D-1引入另一个室中作为掺杂剂。将两种材料以不同的速率进行蒸发,并以15重量%掺杂剂(以基质材料和掺杂剂的总重量为基准计)的掺杂量进行沉积,从而在空穴传输层上形成厚度为30nm的发光层。然后,将2-(4-(9,10-二(萘-2-基)蒽-2-基)苯基)-1-苯基-1H-苯并[d]咪唑引入一个室中,并将8-羟基喹啉合锂(lithium quinolate)(Liq)引入另一个室中。将两种材料以相同的速率进行蒸发,并以50重量%的掺杂量分别进行沉积,以在发光层上形成厚度为30nm的电子传输层。然后,在电子传输层上沉积了厚度为2nm的8-羟基喹啉合锂作为电子注入层之后,通过另一真空气相沉积设备在电子注入层上沉积厚度为150nm的Al阴极。从而,制备了OLED器件。制备OLED器件所用的所有材料,在使用前通过在10-6托条件下的真空升华进行纯化。
制备的OLED器件在3.3V的驱动电压下发射出亮度为1000cd/m2的绿光且电流密度为2.38mA/cm2。
器件实施例2:使用本发明有机电致发光化合物的OLED器件的制造
使用与器件实施例1相同的方法制备OLED器件,不同之处在于使用化合物C-31作为基质材料,使用化合物D-28作为掺杂剂。
制备的OLED器件在3.5V的驱动电压下发射出亮度为1000cd/m2的橙色光且电流密度为2.44mA/cm2。
比较例1:使用常规电致发光化合物制造OLED器件
使用与器件实施例1相同的方法来制备OLED器件,不同之处在于,通过使用4,4’-N,N’-二咔唑-联苯(CBP)作为基质材料并使用化合物D-1作为掺杂剂,在空穴传输层上沉积厚度为30nm的发光层,通过使用二(2-甲基-8-羟基喹啉(quinolinato))(4-苯基苯酚)铝(III)(Balq)沉积厚度为10nm的空穴阻挡层。
制备的OLED器件在4.9V的驱动电压下发射出亮度为1000cd/m2的绿光且电流密度为2.86mA/cm2。
比较例2:使用常规电致发光化合物制造OLED器件
使用与器件实施例1相同的方法来制备OLED器件,不同之处在于,通过使用4,4’-二(咔唑-9-基)-联苯(CBP)作为基质材料并使用化合物D-28作为掺杂剂,在空穴传输层上沉积厚度为30nm的发光层,通过使用二(2-甲基-8-羟基喹啉)(4-苯基苯酚)铝(III)(Balq)沉积厚度为10nm的空穴阻挡层。
制备的OLED器件在4.6V的驱动电压下发射出亮度为1000cd/m2的橙色光且电流密度为3.04mA/cm2。
本发明的有机电致发光化合物比常规材料具有更为优异的发光效率。此外,采用本发明有机电致发光化合物作为基质材料的有机电致发光器件由于低驱动电压和改善的功率消耗而具有高功率效率。
Claims (7)
1.一种由以下通式1表示的有机电致发光化合物:
其中
L1表示单键、取代或未取代的(C6-C30)亚芳基、或取代或未取代的3元至30元杂亚芳基或;
Ar1-Ar5各自独立地表示CR10、C-L2-(L3)m-Ar1或N,前提是Ar1-Ar5中至少一个表示C-L2-(L3)m-Ar1。
L2和L3各自独立地表示取代或未取代的(C6-C30)亚芳基,或取代或未取代的3元至30元杂亚芳基;
R1、R2、R10和Ar1各自独立地表示氢、氘、卤素、取代或未取代的(C1-C30)烷基、取代或未取代的(C3-C30)环烷基、取代或未取代的5元至7元杂环烷基、取代或未取代的(C2-C30)烯基、取代或未取代的(C2-C30)炔基、取代或未取代的(C6-C30)芳基、取代或未取代的3元至30元杂芳基、-NR11R12、-SiR13R14R15、-SR16、-OR17、氰基或硝基;
R11-R17各自独立地表示氢、氘、卤素、取代或未取代的(C1-C30)烷基、取代或未取代的(C6-C30)芳基、或取代或未取代的3元至30元杂芳基;
a表示1-6的整数;当a是等于或大于2的整数时,每一个R1是相同或不同的;
b表示1-4的整数;当b是等于或大于2的整数时,每一个R2是相同或不同的;
m表示1或2的整数;当m是等于或大于2的整数时,每一个L3是相同或不同的;
所述杂亚芳基、杂环烷基和杂芳基含有至少一个选自B、N、O、S、P(=O)、Si和P的杂原子;
前提是R2不是2-咔唑基或3-咔唑基。
2.如权利要求1所述的有机电致发光化合物,其特征在于,所述有机电致发光化合物选自以下通式2-4表示的化合物:
其中
R1、R2、a、b、L1和A1-A5如权利要求1所定义。
3.如权利要求1所述的有机电致发光化合物,其特征在于,所述通式1的L1、L2、L3、R1、R2、R10、Ar1和R11-R17基团中取代的烷基、取代的烯基、取代的炔基、取代的(亚)芳基、取代的杂(亚)芳基、取代的环(亚)烷基和取代的杂环烷基的取代基,各自独立地是至少一个选自以下的基团:氘;卤素;(C1-C30)烷基;卤代(C1-C30)烷基;(C1-C30)烷氧基;(C6-C30)芳氧基;(C6-C30)芳基;3元至30元杂芳基;被(C6-C30)芳基取代的3元至30元杂芳基;被(C1-C30)烷基和(C6-C30)芳基取代的3元至30元杂芳基;(C3-C30)环烷基;5元至7元杂环烷基;三(C1-C30)烷基甲硅烷基;三(C6-C30)芳基甲硅烷基;二(C1-C30)烷基(C6-C30)芳基甲硅烷基;(C1-C30)烷基二(C6-C30)芳基甲硅烷基;(C2-C30)烯基;(C2-C30)炔基;氰基;(C1-C30)烷硫基;(C6-C30)芳硫基;N-咔唑基;单或二(C1-C30)烷基氨基;单或二(C6-C30)芳基氨基;(C1-C30)烷基(C6-C30)芳基氨基;二(C6-C30)芳基硼基;二(C1-C30)烷基硼基;(C1-C30)烷基(C6-C30)芳基硼基;(C6-C30)芳基(C1-C30)烷基;(C1-C30)烷基(C6-C30)芳基;羧基;硝基;和羟基。
4.如权利要求1所述的有机电致发光化合物,其特征在于,所述L1是单键或(C6-C30)亚芳基;而选自以下基团:
其中
L2和L3各自独立地表示(C6-C30)亚芳基或3元至30元杂亚芳基;
R1和R2各自独立地表示氢、氘、卤素、(C1-C30)烷基、(C6-C30)芳基或3元至30元杂芳基;
R10和Ar1各自独立地表示氢、氘、卤素、(C1-C30)烷基、(C3-C30)环烷基、(C6-C30)芳基、3元至30元杂芳基或-SiR13R14R15;
R13-R15各自独立地表示(C1-C30)烷基或(C6-C30)芳基;
a表示0-6的整数;
b表示0-4的整数;
m表示1或2的整数;以及
L1中的亚芳基,L2和L3中的亚芳基和杂亚芳基,R1和R2中的烷基、芳基和杂芳基,R10和Ar1中的烷基、环烷基、芳基和杂芳基,R13-R15中的烷基和芳基各自还可独立地被至少一个选自以下的基团取代:氘、卤素、(C1-C30)烷基、卤代(C1-C30)烷基、(C1-C30)烷氧基、(C6-C30)芳氧基、(C6-C30)芳基、3元至30元杂芳基;被(C6-C30)芳基取代的3元至30元杂芳基;被(C6-C30)芳基和(C1-C30)烷基取代的3元至30元杂芳基;(C3-C30)环烷基;三(C1-C30)烷基甲硅烷基;三(C6-C30)芳基甲硅烷基;二(C1-C30)烷基(C6-C30)芳基甲硅烷基;(C1-C30)烷基二(C6-C30)芳基甲硅烷基;氰基;(C1-C30)烷硫基;(C6-C30)芳硫基;(C6-C30)芳基(C1-C30)烷基;(C1-C30)烷基(C6-C30)芳基。
5.如权利要求1所述的有机电致发光化合物,其特征在于,所述L2表示亚苯基、亚吡啶基、亚芴基、亚咔唑基、亚二苯并呋喃基或亚二苯并噻吩基;L3表示亚苯基、亚联苯基、亚三联苯基、亚萘基、亚吡啶基、亚嘧啶基、亚芴基、亚二苯并呋喃基、亚二苯并噻吩基、亚咔唑基、5H-吡啶并[3,2-b]亚吲哚基或5H-茚并[1,2-b]亚吡啶基;Ar1表示氢、卤素、(C1-C30)烷基、(C3-C30)环烷基、(C6-C30)芳基;3元至30元杂芳基或-SiR13R14R15;R10表示氢或(C6-C30)芳基;R1和R2各自独立地表示氢、卤素、(C1-C30)烷基、(C6-C30)芳基或3元至30元杂芳基;L2中的亚苯基、亚吡啶基、亚芴基、亚咔唑基、亚二苯并呋喃基和亚二苯并噻吩基,L3中的亚苯基、亚联苯基、亚三联苯基、亚萘基、亚吡啶基、亚嘧啶基、亚芴基、亚二苯并呋喃基、亚二苯并噻吩基、亚咔唑基、5H-吡啶并[3,2-b]亚吲哚基和5H-茚并[1,2-b]亚吡啶基,Ar1中的烷基、环烷基、芳基和杂芳基,R10中的芳基,以及R1和R2中的烷基、芳基和杂芳基,各自独立地还可被至少一个选自下组的基团取代:氘、卤素、(C1-C30)烷基、卤代(C1-C30)烷基、(C1-C30)烷氧基、(C6-C30)芳氧基、(C6-C30)芳基、3元至30元杂芳基、被(C6-C30)芳基取代的3元至30元杂芳基、(C1-C30)烷硫基、(C6-C30)芳硫基、(C6-C30)芳基(C1-C30)烷基、和(C1-C30)烷基(C6-C30)芳基。
6.如权利要求1所述的有机电致发光化合物,其特征在于,所述由通式1表示的化合物选自下组:
7.一种包含权利要求1所述的有机电致发光化合物的有机电致发光器件。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020110120860A KR20130055216A (ko) | 2011-11-18 | 2011-11-18 | 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계 발광 소자 |
KR10-2011-0120860 | 2011-11-18 | ||
PCT/KR2012/009654 WO2013073859A1 (en) | 2011-11-18 | 2012-11-15 | Novel organic electroluminescence compounds and organic electroluminescence device comprising the same |
Publications (1)
Publication Number | Publication Date |
---|---|
CN104066728A true CN104066728A (zh) | 2014-09-24 |
Family
ID=48429861
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201280067386.7A Pending CN104066728A (zh) | 2011-11-18 | 2012-11-15 | 新有机电致发光化合物和含有该化合物的有机电致发光器件 |
Country Status (5)
Country | Link |
---|---|
US (1) | US20140316136A1 (zh) |
KR (1) | KR20130055216A (zh) |
CN (1) | CN104066728A (zh) |
TW (1) | TW201331339A (zh) |
WO (1) | WO2013073859A1 (zh) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105684179A (zh) * | 2014-10-01 | 2016-06-15 | 株式会社Lg化学 | 有机发光器件 |
CN109912565A (zh) * | 2017-12-13 | 2019-06-21 | 江苏三月光电科技有限公司 | 一种以氰基氮杂苯为核心的化合物及其在有机电致发光器件中的应用 |
CN109912564A (zh) * | 2017-12-13 | 2019-06-21 | 江苏三月光电科技有限公司 | 一种以氰基氮杂苯为核心的化合物及其在oled器件上的应用 |
CN111051282A (zh) * | 2017-11-16 | 2020-04-21 | 株式会社Lg化学 | 化合物及包含其的有机发光器件 |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP6264877B2 (ja) * | 2012-12-28 | 2018-01-24 | 東ソー株式会社 | 1,2,4−トリス置換ベンゼン化合物、その製造方法、および有機電界発光素子 |
JP6542192B2 (ja) | 2013-03-14 | 2019-07-10 | ザ ブリガム アンド ウィメンズ ホスピタル インコーポレイテッドThe Brigham and Women’s Hospital, Inc. | Bmp阻害剤およびその使用方法 |
JP2017514793A (ja) * | 2014-03-26 | 2017-06-08 | ザ ブリガム アンド ウィメンズ ホスピタル インコーポレイテッドThe Brigham and Women’s Hospital, Inc. | Bmp阻害用組成物及びbmp阻害方法 |
WO2016011019A1 (en) | 2014-07-15 | 2016-01-21 | The Brigham And Women's Hospital, Inc. | Compositions and methods for inhibiting bmp |
KR101864473B1 (ko) * | 2014-09-22 | 2018-06-04 | 주식회사 엘지화학 | 헤테로환 화합물 및 이를 포함하는 유기 발광 소자 |
EP3201187A4 (en) * | 2014-10-01 | 2018-04-11 | The Brigham and Women's Hospital, Inc. | Compositions and methods for inhibiting bmp |
CN109890812B (zh) | 2017-03-27 | 2021-11-23 | 株式会社Lg化学 | 杂环化合物和包含其的有机发光器件 |
WO2020159332A1 (ko) * | 2019-02-01 | 2020-08-06 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
KR102339699B1 (ko) * | 2019-02-01 | 2021-12-15 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
KR102353156B1 (ko) * | 2019-02-01 | 2022-01-19 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
CN113195477A (zh) * | 2019-02-01 | 2021-07-30 | 株式会社Lg化学 | 化合物及包含其的有机发光器件 |
KR102339005B1 (ko) * | 2019-02-01 | 2021-12-14 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
Citations (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20080122344A1 (en) * | 2006-11-24 | 2008-05-29 | Samsung Electronics Co., Ltd. | Organic light emitting compound and organic light emitting device comprising the same, and method of manufacturing the organic light emitting device |
US20080124455A1 (en) * | 2006-11-24 | 2008-05-29 | Samsung Electronics Co., Ltd. | Organic light emitting compound, organic light emitting device comprising the same, and method of manufacturing the organic light emitting device |
KR20110014752A (ko) * | 2009-08-06 | 2011-02-14 | 엘지디스플레이 주식회사 | 적색 인광용 유기전계 발광소자 및 그 제조방법 |
TW201105774A (en) * | 2009-03-31 | 2011-02-16 | Dow Advanced Display Material Ltd | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
TW201120186A (en) * | 2009-08-10 | 2011-06-16 | Gracel Display Inc | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
TW201130805A (en) * | 2009-12-11 | 2011-09-16 | Gracel Display Inc | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
WO2011132865A1 (en) * | 2010-04-20 | 2011-10-27 | Rohm And Haas Electronic Materials Korea Ltd. | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
KR20120036559A (ko) * | 2010-10-08 | 2012-04-18 | 엘지디스플레이 주식회사 | 적색 인광 호스트 물질 및 이를 이용한 유기전계발광소자 |
KR20120038818A (ko) * | 2010-10-14 | 2012-04-24 | 엘지디스플레이 주식회사 | 적색 인광 호스트 물질 및 이를 이용한 유기전계발광소자 |
KR20120081539A (ko) * | 2011-01-11 | 2012-07-19 | (주)씨에스엘쏠라 | 유기발광화합물 및 이를 이용한 유기 광소자 |
WO2012134124A1 (en) * | 2011-03-25 | 2012-10-04 | Rohm And Haas Electronic Materials Korea Ltd. | Novel compounds for organic electronic material and organic electroluminescent device using the same |
KR20120122812A (ko) * | 2011-04-29 | 2012-11-07 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계 발광 소자 |
CN103221406A (zh) * | 2010-09-17 | 2013-07-24 | 罗门哈斯电子材料韩国有限公司 | 新有机电致发光化合物和使用该化合物的有机电致发光器件 |
CN103249800A (zh) * | 2010-10-13 | 2013-08-14 | 罗门哈斯电子材料韩国有限公司 | 用于有机电子材料的新化合物以及使用该化合物的有机电致发光器件 |
-
2011
- 2011-11-18 KR KR1020110120860A patent/KR20130055216A/ko not_active Application Discontinuation
-
2012
- 2012-11-15 CN CN201280067386.7A patent/CN104066728A/zh active Pending
- 2012-11-15 US US14/359,300 patent/US20140316136A1/en not_active Abandoned
- 2012-11-15 WO PCT/KR2012/009654 patent/WO2013073859A1/en active Application Filing
- 2012-11-19 TW TW101143044A patent/TW201331339A/zh unknown
Patent Citations (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20080122344A1 (en) * | 2006-11-24 | 2008-05-29 | Samsung Electronics Co., Ltd. | Organic light emitting compound and organic light emitting device comprising the same, and method of manufacturing the organic light emitting device |
US20080124455A1 (en) * | 2006-11-24 | 2008-05-29 | Samsung Electronics Co., Ltd. | Organic light emitting compound, organic light emitting device comprising the same, and method of manufacturing the organic light emitting device |
TW201105774A (en) * | 2009-03-31 | 2011-02-16 | Dow Advanced Display Material Ltd | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
KR20110014752A (ko) * | 2009-08-06 | 2011-02-14 | 엘지디스플레이 주식회사 | 적색 인광용 유기전계 발광소자 및 그 제조방법 |
TW201120186A (en) * | 2009-08-10 | 2011-06-16 | Gracel Display Inc | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
TW201130805A (en) * | 2009-12-11 | 2011-09-16 | Gracel Display Inc | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
WO2011132865A1 (en) * | 2010-04-20 | 2011-10-27 | Rohm And Haas Electronic Materials Korea Ltd. | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
CN103221406A (zh) * | 2010-09-17 | 2013-07-24 | 罗门哈斯电子材料韩国有限公司 | 新有机电致发光化合物和使用该化合物的有机电致发光器件 |
KR20120036559A (ko) * | 2010-10-08 | 2012-04-18 | 엘지디스플레이 주식회사 | 적색 인광 호스트 물질 및 이를 이용한 유기전계발광소자 |
CN103249800A (zh) * | 2010-10-13 | 2013-08-14 | 罗门哈斯电子材料韩国有限公司 | 用于有机电子材料的新化合物以及使用该化合物的有机电致发光器件 |
KR20120038818A (ko) * | 2010-10-14 | 2012-04-24 | 엘지디스플레이 주식회사 | 적색 인광 호스트 물질 및 이를 이용한 유기전계발광소자 |
KR20120081539A (ko) * | 2011-01-11 | 2012-07-19 | (주)씨에스엘쏠라 | 유기발광화합물 및 이를 이용한 유기 광소자 |
WO2012134124A1 (en) * | 2011-03-25 | 2012-10-04 | Rohm And Haas Electronic Materials Korea Ltd. | Novel compounds for organic electronic material and organic electroluminescent device using the same |
KR20120122812A (ko) * | 2011-04-29 | 2012-11-07 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계 발광 소자 |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105684179A (zh) * | 2014-10-01 | 2016-06-15 | 株式会社Lg化学 | 有机发光器件 |
CN105684179B (zh) * | 2014-10-01 | 2017-09-08 | 株式会社Lg化学 | 有机发光器件 |
US10714692B2 (en) | 2014-10-01 | 2020-07-14 | Lg Chem, Ltd. | Organic light emitting device having a carbazole-based compound formed between cathode and light emitting layer and a spirobifluorene-monoamine based compound formed between anode and light emitting layer |
US11737354B2 (en) | 2014-10-01 | 2023-08-22 | Lg Chem, Ltd. | Organic light emitting device having a carbazole-based compound formed between a cathode and a light emitting layer and a spirobifluorene-monoamine-based compound formed between an anode and a light emitting layer |
CN111051282A (zh) * | 2017-11-16 | 2020-04-21 | 株式会社Lg化学 | 化合物及包含其的有机发光器件 |
CN111051282B (zh) * | 2017-11-16 | 2023-05-09 | 株式会社Lg化学 | 化合物及包含其的有机发光器件 |
CN109912565A (zh) * | 2017-12-13 | 2019-06-21 | 江苏三月光电科技有限公司 | 一种以氰基氮杂苯为核心的化合物及其在有机电致发光器件中的应用 |
CN109912564A (zh) * | 2017-12-13 | 2019-06-21 | 江苏三月光电科技有限公司 | 一种以氰基氮杂苯为核心的化合物及其在oled器件上的应用 |
CN109912564B (zh) * | 2017-12-13 | 2022-08-16 | 江苏三月科技股份有限公司 | 一种以氰基氮杂苯为核心的化合物及其在oled器件上的应用 |
Also Published As
Publication number | Publication date |
---|---|
TW201331339A (zh) | 2013-08-01 |
WO2013073859A1 (en) | 2013-05-23 |
US20140316136A1 (en) | 2014-10-23 |
KR20130055216A (ko) | 2013-05-28 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN104080882B (zh) | 有机电致发光化合物和使用该化合物的有机电致发光器件 | |
CN104066728A (zh) | 新有机电致发光化合物和含有该化合物的有机电致发光器件 | |
CN104271582A (zh) | 新有机电致发光化合物和包含该化合物的有机电致发光器件 | |
CN104039921A (zh) | 新有机电致发光化合物和使用该化合物的有机电致发光器件 | |
CN104066739A (zh) | 新有机电致发光化合物和使用该化合物的有机电致发光器件 | |
CN105579551B (zh) | 有机电致发光化合物和包含所述化合物的有机电致发光装置 | |
CN103619833A (zh) | 用于有机电子材料的新化合物以及使用该化合物的有机电致发光器件 | |
CN108391433A (zh) | 有机电致发光化合物和包含其的有机电致发光装置 | |
CN104053653A (zh) | 新型有机电致发光化合物以及使用该化合物的有机电致发光器件 | |
CN104334682A (zh) | 新颖的有机电致发光化合物和包含该化合物的有机电致发光器件 | |
CN104254529A (zh) | 新有机电致发光化合物和包含该化合物的有机电致发光器件 | |
CN103857673A (zh) | 新有机电致发光化合物和使用该化合物的有机电致发光器件 | |
CN104364345A (zh) | 新有机电致发光化合物和包含该化合物的有机电致发光器件 | |
CN103827119A (zh) | 新颖的有机电致发光化合物和使用该化合物的有机电致发光器件 | |
CN105358654A (zh) | 有机电致发光化合物和包含所述化合物的有机电致发光装置 | |
CN103703003A (zh) | 用于有机电子材料的新化合物以及使用该化合物的有机电致发光器件 | |
CN104271700A (zh) | 新有机电致发光化合物和包含该化合物的有机电致发光器件 | |
CN103732590A (zh) | 用于有机电子材料的新化合物以及使用该化合物的有机电致发光器件 | |
CN108291140B (zh) | 多种主体材料和包含其的有机电致发光装置 | |
CN105189455A (zh) | 有机电致发光化合物和包含所述化合物的有机电致发光装置 | |
CN104245690A (zh) | 新有机电致发光化合物和包含该化合物的有机电致发光器件 | |
CN103534251A (zh) | 用于有机电子材料的新化合物以及使用该化合物的有机电致发光器件 | |
CN105829279A (zh) | 有机电致发光化合物和包含其的有机电致发光装置 | |
CN103889975A (zh) | 苯并咔唑化合物和包含它们的电致发光器件 | |
CN105164120A (zh) | 有机电致发光化合物和包含所述有机电致发光化合物的有机电致发光装置 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20140924 |